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Synthesis 1999; 1999(1): 171-177
DOI: 10.1055/s-1999-3690
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Synthesis of Carbasugars from Aldonolactones: Ritter-Type Epoxide Opening in the Synthesis of Polyhydroxylated Aminocyclopentanes

Steen K. Johansen* , Hanne T. Kornø, Inge Lundt
  • *Department of Organic Chemistry, Technical University of Denmark, Building 201, DK-2800 Lyngby, Denmark; Fax +45 45 93 39 68; E-mail: okil@pop.dtu.dk
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Publikationsdatum:
31. Dezember 1999 (online)

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Using the cis-fused cyclopentane-1,4-lactone, (1R,5S,7R,8R)-7,8-dihydroxy-2-oxabicyclo[3.3.0]oct-3-one (1), as starting material, 5-deoxycarba-β-l-xylo-hexofuranose (6) together with α- (12) and β-1-amino-1,5-dideoxycarba-l-xylo-hexofuranose (16) have been prepared using a number of stereoselective transformations. The key step was the regioselective opening of the epoxide (1R,5S,7R,8R)-7,8-epoxy-2-oxabicyclo-[3.3.0]oct-3-one (4) with different nucleophiles.

polyhydroxy aminocyclopentanes - carbasugars - epoxide ring opening - Ritter reaction